What would the boss think about the idea of taking that $200k and investing it into a cash flowing property or properties, and using that cash flow to pay for your Crest vacation a couple times a year?

I take over single-family mortgages all the time on sub to.

It takes a bit of time but unless you have some great legal advise and follow it precisely, the promised anonymity is not there in most cases. 

So the restriction only allows it to be rented out for half the year correct?  

Bronx properties are on the market for less time compared to last year, with the average days on market (DOM) going from 77 days (in 2023) to 74 days currently.The Bronx neighborhoods with the most househack activity so far in 2024 are:Wakefield (NYC’s northernmost neighborhood!)

Please feel free to comment or connect with me directly.Thank you so much for your time and assistance!

Many times, you may get some referrals there if you're looking to expand your network if you're looking for lending opportunities.

Please be gentle; I'm new at this and it's pretty complex :)Structure / Legal Details- we'd establish market value through a combination of comps from local real estate agent and an appraisal- attorney would establish all required "arms length" aspects including a mortgage at a minimum standard federal rate- LLC would pay us back based on a standard promissory note over 30 yrs Pros of selling to the LLC (I think)- A sale now would be the only time we'd be able to take advantage of the cap gains exclusion on this house bc we won't qualify for the "live there 3 of 5 years" rule due to the timing of our lease and our last time of residence. 

This would be the first time I'm using a HELOC on my primary ($250,000 line) to try and obtain another property.

That's real net cash flow, after all expenses.It takes time and patience.